Heterocycles feature heavily in natural products and molecules of pharmaceutical interest. An economical and diversity oriented synthesis is therefore highly desired. The objective of the proposed research is to develop new atom economical palladium catalyzed C-C bond formation via C-H bond activation of arenes to form benzofurans.This route involves efficient synthesis of the very versatile a-bromo alcohol intermediate, which acts as a precursor to substituted indoles, benzofurans and potentially benzothiophenes. The reaction then proceeds via an exocyclic intermediate which can either be directly isomerized into benzofuran or be further functionalized. For example, it can be oxidized before being trapped by a suitable nucleophile; an asymmetric version of these types of reactions is still to be developed. A variety of benzofurans have been synthesized in good to excellent yields using this methodology.

New C-H functionalization route to heterocycles

240th National Meeting (2010)

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